WO2009089640A1 - Dérivés de diacétyle comme agents aromatisants - Google Patents

Dérivés de diacétyle comme agents aromatisants Download PDF

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Publication number
WO2009089640A1
WO2009089640A1 PCT/CH2009/000015 CH2009000015W WO2009089640A1 WO 2009089640 A1 WO2009089640 A1 WO 2009089640A1 CH 2009000015 W CH2009000015 W CH 2009000015W WO 2009089640 A1 WO2009089640 A1 WO 2009089640A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
diacetyl
methyl
popcorn
Prior art date
Application number
PCT/CH2009/000015
Other languages
English (en)
Inventor
An Minh Lam
Andrew Daniher
Robert G. Eilerman
Philip A. Christenson
Original Assignee
Givaudan Sa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan Sa filed Critical Givaudan Sa
Publication of WO2009089640A1 publication Critical patent/WO2009089640A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2028—Carboxy compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10—Cereal-derived products
    • A23L7/161—Puffed cereals, e.g. popcorn or puffed rice
    • A23L7/174—Preparation of puffed cereals from wholegrain or grain pieces without preparation of meal or dough
    • A23L7/183—Preparation of puffed cereals from wholegrain or grain pieces without preparation of meal or dough by heating without using a pressure release device

Definitions

  • the present invention relates to dioxolanones and dioxanones having the ability to release diacetyl (2,3-butanedione) upon elevated temperature. It further relates to a process of their production and flavour products comprising them.
  • Diacetyl is a well known butter flavour ingredient possessing a sweet, strongly buttery, creamy milky aroma and thus widely-used in butter-flavoured foods.
  • butter-flavoured microwavable popcorn has become extremely popular.
  • n is selected from 0, 1 and 2;
  • R 1 is selected from hydrogen, methyl, ethyl, and propyl (e.g. n-propyl, iso-propyl).
  • the subject compounds are essentially tasteless but release diacetyl (A) and hydroxycarboxylic acid (B, such as lactic acid, 2-hydroxybutyric acid, and 2- hydroxyvaleric acid) upon elevated temperature in the presence of moisture as shown in Scheme 1.
  • A diacetyl
  • B hydroxycarboxylic acid
  • Lactic acid is commonly used as additive in food products. When used in combination with diacetyl it enhances the creamy effect of the overall taste characteristics.
  • a method of generating diacetyl comprising, adding a compound of formula (I) as hereinabove defined, or a mixture thereof, to a food product and subsequently exposing the food product to elevated temperature in the presence of moisture.
  • a method of imparting a butter flavour to a food product comprising, adding a compound of formula (I) as defined hereinabove, or a mixture thereof, to a food product and subsequently exposing the food product to elevated temperature in the presence of moisture.
  • Still another embodiment provides a popcorn product produced by the aforementioned processes.
  • elevated temperature as used herein is meant a temperature higher or equal to about 105 0 C, preferably between about 175°C to about 205 0 C, e.g. 204°C, which may be achieved for example by heating the food product by microwave radiation or by an external heat supplier such as an oven, heating mantle or coil, or flame.
  • moisture as used herein is meant water in an amount from at least 5 weight %, e.g. between about 10 and about 30 weight % based on the food product before heating. This small amount is sufficient enough for releasing diacetyl from a compound of formula (I) when heated. Because almost all food products in its consumable form comprise water the aforementioned ranges is thus not necessary to added further water.
  • popcorn kernels have an internal moisture level of about 11 to about 16 weight %, e.g. a range of 14 - 15% by weight, which is sufficient enough for releasing diacetyl of a compound of formula (I) when heated.
  • the corn kernels may be sprayed with an oily or aqueous composition comprising a compound of formula (I) and optionally other flavourings.
  • flavourings may include salt and/or sugar and other natural and/or artificial flavour ingredients such as artificial butter, cheese flavour, pizza flavors, sweeteners, such as sucralose, savory flavors and other artificial or natural flavorings, such as cinnamon, caramel, apple and coffee, and spices.
  • the composition is typically sprayed onto the corn kernels at room temperature or at a temperature slightly above room temperature, for examples at a temperature from about 15 to 6O 0 C.
  • the corn kernels are packed and sealed in a suitable container such as a bag until the time of use.
  • the oil may be any acceptable food oil, such as palm oil, palm kernel oil, cocoa oil, shea nut oil, partially hydrogenated or fully hydrogenated oils including vegetable oils, sunflower oil, safflower oil, rapeseed oil, cottonseed oil, maize oil, linseed oil, groundnut oil, or soybean oil.
  • Other suitable oils include nut oils (such as almond, brazil nut, cashew, coconut, hazelnut, pecan, peanut, and walnut), olive oil, sesame oil, or flaxseed oil.
  • the oily or aqueous composition may further comprise one or more ingredients or excipients conventionally used in conjunction with popcorn, for example antioxidant, food-grade colorants, and vitamins.
  • the unpopped popcorn products typically comprise from about 600 to about 900 ppm of a compound of formula (I), or a mixture thereof based on the total weight of the flavoured corn kernels.
  • a package comprising popcorn kernels and a flavouring composition comprising a compound of formula (I), or a mixture thereof, for heating in a microwave oven for producing flavoured popped popcorn.
  • the package may take a variety of forms including flexible bags or tube arrangements.
  • the package is preferably microwaveable for placing in a microwave oven.
  • the compounds of formula (I) may be prepared by reacting diacetyl with the appropriate hydroxycarboxylic acid in the presence of an acid, such as trimethylchlorosilane, under conditions known to the person skilled in the art.
  • the compounds of formula (I) are not only suitable for flavouring popcorn, in particular microwave popcorn, but also suitable for flavouring of all kind of food products as long as the product will be heated before consumption, including but not limited to sauces, soups, desserts, cake mixes, bake goods, heat treated beverages, e.g. nutritional drinks, coated cereals and chips.
  • Products such as cereal and chips which do not contain water in its consumable form may be flavoured during processing by admixing an aqueous or oily flavouring composition comprising a compound of formula (I), or a mixture thereof, to the product before drying.
  • the compound of formula (I) may be either pre-solved in a food-grade solvent, such as ethanol, and subsequently further diluted in oil, such as miglyol, or directly admixed with natural and/or artificial flavour ingredients such as artificial butter, cheese flavour, pizza flavors, sweeteners, such as sucralose, savory flavors and other artificial or natural flavorings, such as cinnamon, caramel, apple and coffee, and spices.
  • a food-grade solvent such as ethanol
  • oil such as miglyol
  • natural and/or artificial flavour ingredients such as artificial butter, cheese flavour, pizza flavors, sweeteners, such as sucralose, savory flavors and other artificial or natural flavorings, such as cinnamon, caramel, apple and coffee, and spices.
  • an oily or aqueous solution comprising a compound of formula (I) and at least one flavouring.
  • flavouring composition comprising a compound of formula (I) and at least one flavour ingredient.
  • the flavouring composition typically comprises from about 5 % wt/wt to about 20 % wt/wt of a compound of formula (I).
  • these values are given only by way of example, since the experienced flavourist may also achieve effects or may create novel accords with lower or higher concentrations, e.g. up to about 40% wt/wt weight percent based on the flavouring composition.
  • flavour ingredients which may be particular suitable combined with the compounds of the present invention:
  • flavour ingredients may be found e.g. in "Perfume and Flavor Material of Natural Origin", S. Arctander, Ed., Elizabeth, NJ. , 1960; in “Perfume and Flavor Chemicals”, S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; in “Flavourings”, E. Ziegler and H. Ziegler (ed.), Wiley-VCH
  • Example 1 2.2'.5.5'-tetramethvl-2,2'-bi(1 ,3-dioxolane)-4,4'-dione
  • trimethylchlorosilane (7.4 g, 68 mmol) was added to a solution of diacetyl (6.9 g, 68 mmol) and lactic acid (6 g, 68 mmol) in 60 ml of hexane.
  • the reaction was allowed to stir at room temperature for 16 hours.
  • the crude product was neutralized with a sodium carbonate solution and extracted with MTBE. The extracts were washed with brine, dried over sodium sulfate and concentrated.

Abstract

L'invention porte sur des composés de formule (I) où n est choisi parmi 0, 1 et 2 ; et R1 est choisi parmi hydrogène, méthyle, éthyle et propyle. L'invention porte sur un procédé de production de composés de formule (I) et sur des produits d'arôme les comprenant. Le mode de réalisation préféré est un produit de compensation de diacétyle avec l'acide lactique. Les produits libèrent le diacétyle lors du chauffage et confèrent un arôme butyreux aux produits alimentaires.
PCT/CH2009/000015 2008-01-15 2009-01-13 Dérivés de diacétyle comme agents aromatisants WO2009089640A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1115808P 2008-01-15 2008-01-15
US61/011,158 2008-01-15

Publications (1)

Publication Number Publication Date
WO2009089640A1 true WO2009089640A1 (fr) 2009-07-23

Family

ID=40380477

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH2009/000015 WO2009089640A1 (fr) 2008-01-15 2009-01-13 Dérivés de diacétyle comme agents aromatisants

Country Status (1)

Country Link
WO (1) WO2009089640A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8883235B2 (en) 2011-02-23 2014-11-11 Conagra Foods Rdm, Inc. Ingredient delivery system for popcorn kernels

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0068774A1 (fr) * 1981-06-24 1983-01-05 Hercules Incorporated Précurseurs de dicétones
EP0247646A1 (fr) * 1986-04-25 1987-12-02 Unilever N.V. Composition aromatisante, son utilisation et sa préparation
EP0293957A2 (fr) * 1987-05-14 1988-12-07 Unilever N.V. Usage de précurseurs de dicétone dans les produits alimentaires
WO2006058893A2 (fr) * 2004-12-03 2006-06-08 Symrise Gmbh & Co. Kg Utilisation de diacetyle trimere comme substance aromatique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0068774A1 (fr) * 1981-06-24 1983-01-05 Hercules Incorporated Précurseurs de dicétones
EP0247646A1 (fr) * 1986-04-25 1987-12-02 Unilever N.V. Composition aromatisante, son utilisation et sa préparation
EP0293957A2 (fr) * 1987-05-14 1988-12-07 Unilever N.V. Usage de précurseurs de dicétone dans les produits alimentaires
WO2006058893A2 (fr) * 2004-12-03 2006-06-08 Symrise Gmbh & Co. Kg Utilisation de diacetyle trimere comme substance aromatique

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8883235B2 (en) 2011-02-23 2014-11-11 Conagra Foods Rdm, Inc. Ingredient delivery system for popcorn kernels

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